The invention relates to a method for preparing a toluylene diamine mixture which, along with toluylene diamine (TDA), also contains a high-boiling fraction, such as the high-boiling fraction which is accumulated as a sump flow in the distillative preparation of product mixtures obtained by hydrogenating dinitrotoluene. The method has a step (A), namely preparing a TDA mixture containing, based on the total mass of the mixture, (1) TDA in a range of 5 mass % to 80 mass % and (2) a high-boiling fraction in a range of 20 mass % to 95 mass %; a step (B), namely distilling TDA off from the TDA mixture, thereby obtaining a liquid TDA-depleted method product, containing (1) TDA in a range of 0 mass % to 38 mass % and (2) a high-boiling fraction in a range of 62 mass % to 100 mass %; and a step (C) namely mixing water into the TDA-depleted method product in a mixing chamber, thereby obtaining a mixture mixed with water, wherein the temperature and quantity of the water to be mixed into the mixture and the temperature and quantity of the TDA-depleted method product are matched such that the resulting temperature of the mixture mixed with water ranges from 110° C. to 250° C., and the mixture mixed with water is provided as a single phase. The mixing chamber is supplied with a pressure which is greater than or equal to the water vapor partial pressure at the resulting temperature.

The invention relates to a method for preparing a toluylene diamine mixture which, along with toluylene diamine (TDA), also contains a high-boiling fraction, such as the high-boiling fraction which is accumulated as a sump flow in the distillative preparation of product mixtures obtained by hydrogenating dinitrotoluene. The method has a step (A), namely preparing a TDA mixture containing, based on the total mass of the mixture, (1) TDA in a range of 5 mass % to 80 mass % and (2) a high-boiling fraction in a range of 20 mass % to 95 mass %; a step (B), namely distilling TDA off from the TDA mixture, thereby obtaining a liquid TDA-depleted method product, containing (1) TDA in a range of 0 mass % to 38 mass % and (2) a high-boiling fraction in a range of 62 mass % to 100 mass %; and a step (C) namely mixing water into the TDA-depleted method product in a mixing chamber, thereby obtaining a mixture mixed with water, wherein the temperature and quantity of the water to be mixed into the mixture and the temperature and quantity of the TDA-depleted method product are matched such that the resulting temperature of the mixture mixed with water ranges from 110° C. to 250° C., and the mixture mixed with water is provided as a single phase. The mixing chamber is supplied with a pressure which is greater than or equal to the water vapor partial pressure at the resulting temperature.

A process for preparing trans-enriched MDACH, including: distilling an MDACH starting mixture in the presence of an auxiliary, which is an organic compound having a molar mass of 62 to 500 g/mol, a boiling point at least 5° C. above the boiling point of cis,cis-2,6-diamino-1-methylcyclohexane, and 2 to 4 functional groups, each of which is independently an alcohol group or a primary, secondary or tertiary amino group. The MDACH starting mixture includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, based on the total amount of MDACH present in the MDACH starting mixture. The MDACH starting mixture includes both trans and cis isomers. Trans-enriched MDACH includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, where the proportion of trans isomers in the mixture is higher than the proportion of trans isomers in the MDACH starting mixture.

A process for preparing trans-enriched MDACH, including: distilling an MDACH starting mixture in the presence of an auxiliary, which is an organic compound having a molar mass of 62 to 500 g/mol, a boiling point at least 5° C. above the boiling point of cis,cis-2,6-diamino-1-methylcyclohexane, and 2 to 4 functional groups, each of which is independently an alcohol group or a primary, secondary or tertiary amino group. The MDACH starting mixture includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, based on the total amount of MDACH present in the MDACH starting mixture. The MDACH starting mixture includes both trans and cis isomers. Trans-enriched MDACH includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, where the proportion of trans isomers in the mixture is higher than the proportion of trans isomers in the MDACH starting mixture.

Provided herein are methods and intermediates for making (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.

Provided herein are methods and intermediates for making (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.

Provided herein are methods and intermediates for making (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.

Provided herein are methods and intermediates for making (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.

Provided herein are methods and intermediates for making (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.

Provided herein are methods and intermediates for making (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.